Abstract

CUEVAS YANEZ, Erick; ARCEO DE LA PENA, Abraham; MUCHOWSKI, Joseph M.  and  CRUZ ALMANZA, Raymundo. Synthesis and Properties of 2-diazo-1-[2-(thiophen-2-ylmethoxy)-phenyl]-ethanone. Intramolecular Cyclization Through a Carbenoid Intermediate. Rev. Soc. Quím. Méx [online]. 2003, vol.47, n.2, pp.202-206. ISSN 0583-7693.

The synthesis of 2-diazo-1-[2-(thiophen-2-ylmethoxy)-phenyl]-ethanone (1) is described. The procedure involves an aromatic nucleophilic substitution between the sodium 2-thiophenyl methoxide and 2-fluorobenzaldehyde, the subsequent mild-condition oxidation to the corresponding carboxylic acid, and final transformation through carbonic-carboxylic anhydride intermediate to the a-diazoketone. Treatment of compound 1 with catalytic amounts of rhodium (II) acetate gives the thienylmethyl benzofuranone 10 which comes from the [2,3] sigmatropic rearrangement of the oxonium ylide 9 derived from the rhodium carbenoid that is postulated as reaction intermediate key.

Keywords : α-diazoketones; cyclization; rhodium carbenoid.

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